Water → HCID 57616394, compound

HRID 2354301Notes

Reaction equation

HRID 2354301 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[C:24]1[C:32]2[C:27](=[C:28]([Cl:33])[CH:29]=[CH:30][CH:31]=2)[N:26]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43]OS(C)(=O)=O)=[CH:37][CH:36]=2)[CH:25]=1)(=O)C.[N-:49]=[N+]=[N-].[Na+].O>CN(C)C=O>[NH2:49][CH2:43][CH2:42][O:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][N:26]2[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:33])[C:24]([C@@H:6]3[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]3[OH:4])=[CH:25]2)=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86628793HCID 86628793, compound

Product 1

HCID 57616394HCID 57616394, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-7-chloro-1-{4-[2-(methanesulfonyloxy)ethoxy]-benzyl}-1H-indole (85 mg) in N,N-dimethylformamide (2 mL) was added sodium azide (12 mg), and the mixture was stirred at 100° C. for 2 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was dissolved in a mixed solvent of methanol (2 mL) and tetra hydrofuran (3 mL). To the solution was added sodium methoxide (28% methanol solution, 0.30 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethylacetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was dissolved in tetra hydrofuran (3 mL). To the solution were added water (0.3 mL) and triphenylphosphine (36 mg), and the mixture was stirred at room temperature for 3 days. The solvent was removed under reduced pressure, and the residue was purified by preparative reverse phase column chromatography (Shiseido CAPCELL PAK C18 ODS, UG80, 5 μm, 20×50 mm, linear gradient water/methanol=90/10-10/90, flow rate 30 mL/min) to give the title compound (12 mg).

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe extract was washed with water and brine successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in a mixed solvent of methanol (2 mL) and tetra hydrofuran (3 mL)
  6. additionTo the solution was added sodium methoxide (28% methanol solution, 0.30 mL)
  7. stirringthe mixture was stirred at room temperature for 30 minutes
  8. additionThe reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution
  9. extractionthe resulting mixture was extracted with ethylacetate
  10. washThe extract was washed with brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was removed under reduced pressure
  13. dissolutionThe residue was dissolved in tetra hydrofuran (3 mL)
  14. additionTo the solution were added water (0.3 mL) and triphenylphosphine (36 mg)
  15. stirringthe mixture was stirred at room temperature for 3 days
  16. customThe solvent was removed under reduced pressure
  17. customthe residue was purified by preparative reverse phase column chromatography (Shiseido CAPCELL PAK C18 ODS, UG80, 5 μm, 20×50 mm, linear gradient water/methanol=90/10-10/90, flow rate 30 mL/min)

Sources & evidence

ORD record
ord-e09bb5a484cd4be4b15a7b5327f46ad6
Source dataset
uspto-grants-2010_07
Patent number
US07750145B2

Reaction notes

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